4-Chloro-N'-(2-hydroxy-benzyl-idene)benzohydrazide monohydrate.

The asymmetric unit of the title compound, C(14)H(11)ClN(2)O(2)·H(2)O, contains a Schiff base mol-ecule and a water mol-ecule of crystallization. The dihedral angle between the two aromatic rings is 27.3 (4)°. In the crystal structure, mol-ecules are linked into a two-dimensional network parallel to the bc plane by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds involving the water mol-ecules.

Related literature

For general background on Schiff bases derived from condensation of aldehydes with benzohydrazides, see: Fun et al. (2008 ▶); Alhadi et al. (2008 ▶); Ali et al. (2007 ▶); Zou et al. (2004 ▶); Shan et al. (2008 ▶); Bedia et al. (2006 ▶); Terzioglu & Gürsoy (2003 ▶). For related structures, see: Nie (2008 ▶); He (2008 ▶); Shi et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H11ClN2O2·H2O

M = 292.71

Monoclinic,

a = 22.397 (3) Å

b = 4.853 (2) Å

c = 12.642 (3) Å

β = 97.15 (3)°

V = 1363.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 298 (2) K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.937, T max = 0.945

10537 measured reflections

2946 independent reflections

1251 reflections with I > 2σ(I)

R int = 0.106

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.214

S = 0.99

2946 reflections

191 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024471/ci2647sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024471/ci2647Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H11ClN2O2·H2O	F000 = 608
Mr = 292.71	Dx = 1.426 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 600 reflections
a = 22.397 (3) Å	θ = 2.6–24.5º
b = 4.853 (2) Å	µ = 0.29 mm−1
c = 12.642 (3) Å	T = 298 (2) K
β = 97.15 (3)º	Block, colourless
V = 1363.4 (7) Å3	0.23 × 0.20 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2946 independent reflections
Radiation source: fine-focus sealed tube	1251 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.106
T = 298(2) K	θmax = 27.0º
ω scans	θmin = 0.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −28→28
Tmin = 0.937, Tmax = 0.945	k = −6→6
10537 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.214	w = 1/[σ2(Fo2) + (0.0902P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
2946 reflections	Δρmax = 0.27 e Å−3
191 parameters	Δρmin = −0.27 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	0.02717 (6)	1.4002 (3)	0.66329 (12)	0.0731 (5)
N2	0.24096 (15)	0.4463 (8)	0.6210 (3)	0.0392 (9)
C8	0.21035 (19)	0.5999 (9)	0.5457 (3)	0.0412 (11)
N1	0.28603 (15)	0.2706 (7)	0.5952 (3)	0.0420 (10)
O2	0.21956 (14)	0.5852 (6)	0.4508 (2)	0.0538 (9)
C9	0.16460 (18)	0.7918 (8)	0.5783 (3)	0.0365 (10)
C14	0.16219 (18)	0.8667 (9)	0.6822 (3)	0.0426 (12)
H14	0.1893	0.7895	0.7359	0.051*
C1	0.35917 (19)	−0.0643 (9)	0.6600 (3)	0.0415 (11)
C7	0.31165 (18)	0.1242 (9)	0.6720 (3)	0.0428 (12)
H7	0.2987	0.1416	0.7388	0.051*
O1	0.36902 (17)	0.0745 (9)	0.4810 (3)	0.0779 (12)
H1	0.3447	0.1897	0.4963	0.117*
C11	0.0808 (2)	1.0889 (10)	0.5252 (4)	0.0537 (13)
H11	0.0531	1.1631	0.4720	0.064*
C12	0.07965 (19)	1.1639 (9)	0.6292 (4)	0.0457 (12)
C13	0.1200 (2)	1.0561 (10)	0.7088 (4)	0.0512 (13)
H13	0.1191	1.1086	0.7793	0.061*
C2	0.3871 (2)	−0.0802 (11)	0.5669 (4)	0.0536 (13)
C10	0.12292 (19)	0.9047 (10)	0.4998 (3)	0.0466 (12)
H10	0.1236	0.8543	0.4290	0.056*
C6	0.3802 (2)	−0.2325 (10)	0.7435 (4)	0.0577 (14)
H6	0.3624	−0.2236	0.8060	0.069*
C4	0.4539 (2)	−0.4315 (13)	0.6486 (5)	0.0726 (17)
H4	0.4851	−0.5558	0.6443	0.087*
C5	0.4271 (2)	−0.4144 (11)	0.7380 (5)	0.0656 (15)
H5	0.4402	−0.5255	0.7962	0.079*
C3	0.4344 (2)	−0.2616 (12)	0.5632 (5)	0.0739 (17)
H3	0.4536	−0.2697	0.5021	0.089*
O3	0.23525 (17)	0.0885 (7)	0.3450 (2)	0.0568 (9)
H2	0.236 (2)	0.445 (11)	0.6905 (12)	0.080*
H3B	0.245 (2)	−0.049 (5)	0.385 (3)	0.080*
H3A	0.235 (2)	0.234 (5)	0.381 (3)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0598 (8)	0.0587 (9)	0.1059 (12)	0.0176 (7)	0.0301 (8)	0.0051 (9)
N2	0.042 (2)	0.044 (2)	0.0329 (19)	0.0072 (18)	0.0065 (17)	0.002 (2)
C8	0.044 (3)	0.040 (3)	0.039 (3)	0.000 (2)	0.003 (2)	0.004 (2)
N1	0.041 (2)	0.042 (2)	0.044 (2)	0.0057 (19)	0.0121 (18)	−0.006 (2)
O2	0.078 (2)	0.050 (2)	0.0345 (18)	0.0109 (18)	0.0142 (16)	0.0034 (16)
C9	0.038 (2)	0.030 (3)	0.041 (3)	−0.002 (2)	0.005 (2)	0.003 (2)
C14	0.045 (3)	0.046 (3)	0.035 (3)	0.005 (2)	−0.001 (2)	0.004 (2)
C1	0.037 (2)	0.038 (3)	0.049 (3)	−0.001 (2)	0.003 (2)	−0.007 (2)
C7	0.044 (3)	0.052 (3)	0.033 (2)	0.005 (2)	0.005 (2)	−0.001 (2)
O1	0.084 (3)	0.098 (3)	0.054 (2)	0.030 (2)	0.0195 (19)	0.002 (2)
C11	0.050 (3)	0.058 (3)	0.053 (3)	0.001 (3)	0.001 (2)	0.005 (3)
C12	0.040 (2)	0.033 (3)	0.065 (3)	0.004 (2)	0.010 (2)	0.007 (2)
C13	0.053 (3)	0.051 (3)	0.050 (3)	0.006 (3)	0.010 (2)	−0.001 (3)
C2	0.051 (3)	0.061 (4)	0.048 (3)	0.009 (3)	0.004 (2)	−0.005 (3)
C10	0.044 (3)	0.054 (3)	0.041 (3)	0.007 (3)	0.003 (2)	0.004 (3)
C6	0.050 (3)	0.055 (3)	0.066 (3)	0.003 (3)	−0.002 (3)	−0.005 (3)
C4	0.051 (3)	0.068 (4)	0.096 (5)	0.019 (3)	−0.001 (3)	−0.024 (4)
C5	0.063 (4)	0.050 (4)	0.077 (4)	−0.001 (3)	−0.019 (3)	−0.002 (3)
C3	0.064 (4)	0.078 (4)	0.083 (4)	0.017 (3)	0.020 (3)	−0.025 (4)
O3	0.091 (2)	0.047 (2)	0.0328 (17)	−0.007 (2)	0.0107 (17)	−0.0014 (17)

Cl1—C12	1.735 (4)	C11—C10	1.366 (6)
N2—C8	1.330 (5)	C11—C12	1.367 (6)
N2—N1	1.391 (5)	C11—H11	0.93
N2—H2	0.899 (10)	C12—C13	1.370 (6)
C8—O2	1.245 (5)	C13—H13	0.93
C8—C9	1.481 (6)	C2—C3	1.384 (7)
N1—C7	1.280 (5)	C10—H10	0.93
C9—C14	1.370 (6)	C6—C5	1.380 (7)
C9—C10	1.388 (6)	C6—H6	0.93
C14—C13	1.390 (6)	C4—C5	1.346 (7)
C14—H14	0.93	C4—C3	1.386 (7)
C1—C6	1.371 (6)	C4—H4	0.93
C1—C2	1.401 (6)	C5—H5	0.93
C1—C7	1.426 (6)	C3—H3	0.93
C7—H7	0.93	O3—H3B	0.85 (3)
O1—C2	1.340 (5)	O3—H3A	0.84 (3)
O1—H1	0.82
C8—N2—N1	120.0 (3)	C11—C12—Cl1	120.7 (4)
C8—N2—H2	126 (3)	C13—C12—Cl1	118.3 (4)
N1—N2—H2	114 (3)	C12—C13—C14	118.8 (4)
O2—C8—N2	121.7 (4)	C12—C13—H13	120.6
O2—C8—C9	120.5 (4)	C14—C13—H13	120.6
N2—C8—C9	117.8 (4)	O1—C2—C3	119.0 (5)
C7—N1—N2	115.6 (3)	O1—C2—C1	121.9 (4)
C14—C9—C10	118.5 (4)	C3—C2—C1	119.1 (5)
C14—C9—C8	123.0 (4)	C11—C10—C9	120.8 (4)
C10—C9—C8	118.4 (4)	C11—C10—H10	119.6
C9—C14—C13	121.1 (4)	C9—C10—H10	119.6
C9—C14—H14	119.5	C1—C6—C5	122.2 (5)
C13—C14—H14	119.5	C1—C6—H6	118.9
C6—C1—C2	117.9 (4)	C5—C6—H6	118.9
C6—C1—C7	119.3 (4)	C5—C4—C3	119.1 (5)
C2—C1—C7	122.8 (4)	C5—C4—H4	120.4
N1—C7—C1	123.0 (4)	C3—C4—H4	120.4
N1—C7—H7	118.5	C4—C5—C6	120.3 (5)
C1—C7—H7	118.5	C4—C5—H5	119.9
C2—O1—H1	109.5	C6—C5—H5	119.9
C10—C11—C12	119.8 (4)	C2—C3—C4	121.4 (5)
C10—C11—H11	120.1	C2—C3—H3	119.3
C12—C11—H11	120.1	C4—C3—H3	119.3
C11—C12—C13	121.0 (4)	H3B—O3—H3A	111 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.84 (3)	1.97 (3)	2.800 (4)	170 (5)
O3—H3B···O2i	0.85 (3)	2.07 (3)	2.828 (4)	149 (5)
N2—H2···O3ii	0.90 (1)	1.96 (1)	2.856 (4)	172 (5)
O1—H1···N1	0.82	1.96	2.667 (5)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2	0.84 (3)	1.97 (3)	2.800 (4)	170 (5)
O3—H3B⋯O2i	0.85 (3)	2.07 (3)	2.828 (4)	149 (5)
N2—H2⋯O3ii	0.90 (1)	1.96 (1)	2.856 (4)	172 (5)
O1—H1⋯N1	0.82	1.96	2.667 (5)	143

Symmetry codes: (i) ; (ii) .